N,N'-Dimethylethylenediamine → HCID 67528572, compound

HRID 1867552Notes

Reaction equation

HRID 1867552 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][N:18]=2)[CH:13]=[CH:12]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[N:11]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=2)[C:19]2=[N:18][CH:17]=[CH:16][CH:15]=[C:14]2[CH:13]=[CH:12]1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 62657Potassium Phosphate, TribasicHCID 30407702-(4-Iodophenyl)ethan-1-ol

Product 1

HCID 67528572HCID 67528572, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.24 g (5 mmol) of 2-(4-iodophenyl)ethanol, 0.62 g (5.25 mmol) of 7-azaindole, 2.33 g (11.0 mmol) of potassium phosphate, 0.082 g (1.0 mmol) of N,N′-dimethylethylenediamine and 0.095 g (0.50 mmol) of cuprous iodide in 4 ml of toluene is heated at 80° C. overnight with thorough stirring under an argon atmosphere. The mixture is cooled to ambient temperature and diluted with 150 ml of ethyl acetate and 50 ml of water. After the phases have settled and been separated, the organic phase is washed with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 70/30 then 60/40 and 50/50 mixture of cyclohexane and ethyl acetate, to give 1.05 g of product in the form of an oil.

Workup

  1. temperatureThe mixture is cooled to ambient temperature
  2. custombeen separated
  3. washthe organic phase is washed with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution
  4. dry with materialIt is dried over sodium sulphate
  5. customevaporated to dryness
  6. customThe residue is purified by chromatography on silica gel
  7. washeluting with a 70/30
  8. addition60/40 and 50/50 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-8bf403d14b674a44b53be3519ba88f13
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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